Trifluoroacetic acid → HCID 86659576, compound

HRID 403020Notes

Reaction equation

HRID 403020 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:69]=[CH:68][C:13]([O:14][CH2:15][C@@H:16]([CH2:42][O:43][C:44](=[O:67])[C@H:45]([CH3:66])[NH:46][C:47](=[O:65])[CH2:48][C@H:49]([NH:57]C(OC(C)(C)C)=O)[C:50]([O:52]C(C)(C)C)=[O:51])[O:17][C:18](=[O:41])[C@H:19]([CH3:40])[NH:20][C:21](=[O:39])[CH2:22][C@H:23]([NH:31]C(OC(C)(C)C)=O)[C:24]([O:26]C(C)(C)C)=[O:25])=[CH:12][CH:11]=2)[C:5]([C:70]#[N:71])=[C:4]([S:72][CH2:73][C:74]2[N:75]=[C:76]([C:79]3[CH:84]=[CH:83][C:82]([Cl:85])=[CH:81][CH:80]=3)[O:77][CH:78]=2)[N:3]=1.[F:86][C:87]([F:92])([F:91])[C:88]([OH:90])=[O:89]>ClCCl>[F:86][C:87]([F:92])([F:91])[C:88]([OH:90])=[O:89].[F:86][C:87]([F:92])([F:91])[C:88]([OH:90])=[O:89].[NH2:31][C@@H:23]([CH2:22][C:21](=[O:39])[NH:20][C@@H:19]([CH3:40])[C:18](=[O:41])[O:17][C@@H:16]([CH2:15][O:14][C:13]1[CH:12]=[CH:11][C:10]([C:6]2[C:5]([C:70]#[N:71])=[C:4]([S:72][CH2:73][C:74]3[N:75]=[C:76]([C:79]4[CH:80]=[CH:81][C:82]([Cl:85])=[CH:83][CH:84]=4)[O:77][CH:78]=3)[N:3]=[C:2]([NH2:1])[C:7]=2[C:8]#[N:9])=[CH:69][CH:68]=1)[CH2:42][O:43][C:44](=[O:67])[C@H:45]([CH3:66])[NH:46][C:47](=[O:65])[CH2:48][C@H:49]([NH2:57])[C:50]([OH:52])=[O:51])[C:24]([OH:26])=[O:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86659578HCID 86659578, compound

Product 1

HCID 86659576HCID 86659576, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An amount of 190 mg (0.156 mmol) of the compound from example 22A was introduced in 1 ml of dichloromethane, admixed with 0.120 ml (1.559 mmol) of trifluoroacetic acid and stirred at RT overnight. The reaction mixture was then concentrated and the residue was purified by means of preparative HPLC (eluent gradient: acetonitrile/water 10:90→95:5 with addition of 0.1% TFA). This gave 76 mg (43% of theory) of the target compound.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customthe residue was purified by means of preparative HPLC (eluent gradient: acetonitrile/water 10:90→95:5 with addition of 0.1% TFA)

Sources & evidence

ORD record
ord-caacdcb3fbc343b280579057f081da91
Source dataset
uspto-grants-2014_06
Patent number
US08741834B2

Reaction notes

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